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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
New Downtown Annapolis Condo With Free Parking
2 bedrooms, 2 beds, 2 private bathrooms
15–20 Nov
,
4.98 out of 5 average rating, 165 reviews
Superhost
Home in Annapolis
Annapolis Charmer - Perfect Location
3 bedrooms, 3 beds
13–18 Sept
New place to stay
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
3–8 Dec
4.97 out of 5 average rating, 462 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
3–8 Oct
4.97 out of 5 average rating, 471 reviews
Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds
29 Oct – 3 Nov
4.96 out of 5 average rating, 228 reviews
Guest favourite
Home in Annapolis
Admiral’s Landing: Walk to Naval Academy, West St.
3 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 53 reviews
Guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 82 reviews
Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds
13–18 Sept
4.94 out of 5 average rating, 54 reviews
Guest favourite
Home in Annapolis
Charming Renovated Historic Home Downtown wParking
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.91 out of 5 average rating, 242 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
25–30 Oct
4.91 out of 5 average rating, 121 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
1–6 Nov
4.92 out of 5 average rating, 1137 reviews
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
1–6 Jan
4.96 out of 5 average rating, 263 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 226 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 175 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
25–30 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Guest suite in Arnold
Captains Quarters Oasis Near Annapolis, Sleeps 4
1 bedroom, 2 beds
13–18 Sept
4.95 out of 5 average rating, 215 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
11–16 Sept
5.0 out of 5 average rating, 147 reviews
Guest favourite
Flat in Annapolis
The USNA Getaway!
1 bedroom, 3 beds
13–18 Sept
4.9 out of 5 average rating, 80 reviews